The first parade was organized on Saturday, June 27, 1970, as a march[1] from Washington Square Park ("Bughouse Square") to the Water Tower at the intersection of Michigan and Chicago avenues, which was the route originally planned, and then many of the participants extemporaneously marched on to the Civic Center (now Richard J. Daley) Plaza.[2] Today the parade takes place through the main streets of Lake View East, a neighborhood enclave of the Lakeviewcommunity area. Recent parades have started at noon on Halsted Street, proceeding north from Belmont Avenue, passing the Center on Halsted at Waveland Avenue; south on Broadway (at Grace Street) to Diversey Parkway and east on Diversey Parkway to Cannon Drive. The parade route will begin in the Uptown neighborhood at the corner of Broadway and Montrose. The parade will then proceed south down Broadway to Halsted, continue south on Halsted to Belmont, then east on Belmont to Broadway where it will resume its former route.

With the increasing political participation of gay, lesbian, bisexual and transgender Americans and the community's relatively high financial resources through political action groups and as individual donors, Illinois politicians have increased their presence at the Chicago Pride Parade. Both the Illinois Democratic and Republican parties have been heavily represented, most noticeably by former GovernorRod Blagojevich, a Democrat, and former TreasurerJudy Baar Topinka, a Republican. Both had strong support from many gay and lesbian voters.

On June 28, 2009 more than 500,000 spectators watched the 40th annual Chicago Pride Parade. Among the entries were several marching bands, dance troupes, twirlers, and many political figures. The 2010 parade featured an appearance from the Chicago Blackhawks' Brent Sopel and The Stanley Cup as part of the Chicago Gay Hockey Association's float. Sopel appeared in the parade to honor Brendan Burke, the gay son of the Maple Leafs' GM Brian Burke. The 2011 parade included 250 entries and was attended by over 800,000 spectators, almost double the previous year, causing massive overcrowding and resulted in a reorganization of the parade route for the 2012 parade.

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June 28, 1970: (1st) Attendance: 150-200 Parade Route: Bughouse Square, down Dearborn to Chicago Avenue, east to the Water Tower, then south on Michigan Avenue to the Civic Center (now Daley Plaza)[1]

June 27, 1971: (2nd) Attendance: 1000 Parade Route: Diversey Harbor, going west to Clark Street, then south to the Free Forum at LaSalle Street [2]

June 25, 1972: (3rd) Attendance:

June 24, 1973: (4th) Attendance:

June 30, 1974: (5th) Attendance:

June 29, 1975: (6th) Attendance:

June 27, 1976: (7th) Attendance:

June 26, 1977: (8th) Attendance: 3000 Parade Route: Halsted and Addison, going east to Broadway, south to Clark, then south on Clark to Fullerton, east on Fullerton to Stockton Drive, and finally south on Stockton to the Lincoln Park Free Foru [3]

As the Chicago Pride Parade is held on the last Sunday in June (except for in 1994), weather for the event is usually warm and dry. The average high temperature at O'Hare airport for parade day since 1970 is 83 degrees and the average low is 61. Additionally, on 22% of parade days there has been measurable precipitation. The warmest pride parade was 99 degrees in 1983. The wettest was in 1978 when 0.92 inches of rain fell.